EP0085476B1 - Sulfonamides à activité herbicide - Google Patents

Sulfonamides à activité herbicide Download PDF

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Publication number
EP0085476B1
EP0085476B1 EP83300078A EP83300078A EP0085476B1 EP 0085476 B1 EP0085476 B1 EP 0085476B1 EP 83300078 A EP83300078 A EP 83300078A EP 83300078 A EP83300078 A EP 83300078A EP 0085476 B1 EP0085476 B1 EP 0085476B1
Authority
EP
European Patent Office
Prior art keywords
och
compounds
formula
benzenesulfonamide
aminocarbonyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
EP83300078A
Other languages
German (de)
English (en)
Other versions
EP0085476A3 (en
EP0085476A2 (fr
Inventor
Richard Frank Sauers
Rafael Shapiro
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US06/437,325 external-priority patent/US4494980A/en
Priority claimed from US06/437,367 external-priority patent/US4460401A/en
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Priority to AT83300078T priority Critical patent/ATE26715T1/de
Publication of EP0085476A2 publication Critical patent/EP0085476A2/fr
Publication of EP0085476A3 publication Critical patent/EP0085476A3/en
Application granted granted Critical
Publication of EP0085476B1 publication Critical patent/EP0085476B1/fr
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D521/00—Heterocyclic compounds containing unspecified hetero rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/32—Sulfur atoms
    • C07D213/34—Sulfur atoms to which a second hetero atom is attached
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Definitions

  • Sulfonamides containing a tetrahydrothiophene or tetrahydrothiopyran group can also be prepared by the sequence of reactions shown in Equation 9. wherein
  • the salt XVIII is then immediately treated with one equivalent of a chloro- or bromoaldehyde of Formula XXI at -70° to -80°.
  • the temperature is raised to 25° for 1 to 3 days, and the reaction is then quenched by the addition of an acid such as acetic acid.
  • the pure product, XIX is isolated by stripping off the solvent and chromatographing or recrystallizing the crude product.
  • chloramine is prepared at 0° by the addition of aqueous sodium hypochlorite to a stirred mixture of 30% ammonium hydroxide solution and diethyl ether.
  • the lithium sulfinates of Formula XXIII are added to this mixture at 0° and the resulting mixture stirred at room temperature for 2-24 hours.
  • the product sulfonamides are isolated by extraction into a solvent such as ethyl acetate and evaporation of the solvent.
  • the sulfonamides of Formula Ilk may be purified by recrystallization from solvents such as ethanol, 1-chlorobutane, or acetonitrile, or by column chromatography.
  • the active ingredient is blended with-attapulgite and then passed through a hammer-mill to produce particles substantially all below 200 microns.
  • the ground concentrate is then blended with powdered pyrophyllite until homogeneous.

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Control Or Security For Electrophotography (AREA)

Claims (20)

1. Un composé de la formule
Figure imgb0225
où
Q est
Figure imgb0226
Figure imgb0227
Figure imgb0228
ou Q' est
Figure imgb0229
Figure imgb0230
Figure imgb0231
W est O ou S;
W' est O ou S;
R est H, F, Cl, CH3 ou OCH3;
R1 est H, F, CI, Br, CH3, CF3 ou OCH3;
R2, R3, R5, R9, R10, R11, R12 et R17 sont indépendamment H ou CH3;
R4, R6, R7 et R8 sont indépendamment H, CH3 ou OCH3;
R13, R14, R15 et R16 sont indépendamment CH3 ou OCH3;
R18 est H ou CH3;
R19 est H ou CH3;
R20 est H ou CH3;
R21 est H ou CH3;
R22 est H ou CH3;
R23 est H ou CH3;
R24 est H, CH3, C2H5, CI, Br, OCH3 ou OC2H5;
R25 est H, CH3, C2H5, CI, Br, OCH3 ou OC2H15;
R26 est H, CH3, C2H5, CI, Br, OCH3, OC2H5 ou CO2CH3;
R27 est H ou CH3;
R28 est H ou CH3;
A est
Figure imgb0232
X est CH3, OCH3 ou CI;
Y est CH3, C2H5, CH2OCH3, OCH3, OC2H5, CH(OCH3)2, SCH3, CF3, NH2, NHCH3, N(CH3)2; OCH2CH2OCH3, OCH2CF3 ou
Figure imgb0233
Y1 est CH3, C2H5, CH2OCH3, OCH3, OC2H5, CH(OCH3)2, NH2, NHCH3 ou N(CH3)2;
Z est CH ou N;
X1 est CH3 OCH3 ou CI;
G est O ou CH2;
X2 est C1―C3 alkyle ou CH2CF3;
Y2 est CH3O, C2H5O, CH3S ou C2H5S;

et leurs sels convenant pour l'agriculture;
avec les conditions que:
1) quand W est S, alors R17 est H,
A est
Figure imgb0234
Y est CH3, OCH3, C2H5, CH2OCH3, CH(OCH3)2 ou
Figure imgb0235
2) quand Q est
Figure imgb0236
alors R24 est H, CH3 ou C2H5; R25 est H, CH3 ou C2H5; et R26 est H, CH3, C2H5 ou ―CO2CH3;
3) quand l'un de R24, R25, R26 est autre que H, alors les deux autres substituants sont H ou CH3;
4) le nombre total d'atomes de carbone dans R18, R19, R20; R21; R22; R23; R27 et R28 est inférieur ou égal à 4;
5) quand X est CI, alors Z est CH et Y ou Y1 est OCH3, NH2, OC2H5, NHCH3 ou N(CH3)2; et
6) quand R est CH3, alors R est dans la position 3,4 ou 5 du noyau benzénique, par rapport au groupe sulfonamide dans la position 1.
2. Les composés selon la revendication 1, formule I, dans lesquels W est O.
3. Les composés selon la revendication 2, dans lesquels R1 et R17 sont H.
4. Les composés selon la revendication 3, dans lesquels R24 est H, CH3 ou C2H5; R25 est H, CH3 ou C2H5; et R26 est H, CH3, C2H5 ou ―CO2CH3.
5. Les composés selon la revendication 4, dans lesquels Y est CH3, CH2OCH3, OCH3, OC2H5, CH(OCH3)2 ou
Figure imgb0237
et A est
Figure imgb0238
6. Les composés selon la revendication 1, formula la, dans lesquels R et R17 sont H.
7. Les composés selon la revendication 6, dans lesquels Y1 est CH3, OCH3, CH2OCH3 ou N(CH3)2.
8. Les composés selon la revendication 4, dans lesquels W' est O.
9. Les composés selon la revendication 4, dans lesquels W' est S.
10. Les composés selon la revendication 7, dans lesquels Q' est une pyridine substituée.
11. Les composés selon la revendication 7, dans lesquels Q' est une pyrimidine substituée.
12. Les composés selon la revendication 7, dans lesquels Q' est un pyrazine substituée.
13. Les composés selon la revendication 7, dans lesquels Q' est une triazine substituée.
14. Les composé selon la revendication 1, choisi parmi le N - [(4,6 - diméthylpyrimidin - 2 - yl)-aminocarbonyl] - 2 - (tétrahydrofuran - 2 - yl)benzènesulfonamide; le N - [(4 - méthoxy - 6 - méthyle- pyrimidin - 2 - yl)aminocarbonyl] - 2 - (tétrahydrofuran - 2 - yl)benzènesulfonamide; le N - [(4,6 - diméthoxypyrimidin - 2 - yl)aminocarbonyl] - 2 - (tétrahydrofuran - 2 - yl)benzènesulfonamide; le N - [(4 - chloro - 6 - méthoxypyrimidin - 2 - yl)aminocarbonyl] - 2 - (tétrahydrofuran - 2 - yl)-benzènesulfonamide; le N - [(4,6 - diméthoxy - 1,3,5 - triazin - 2 - yl)aminocarbonyl] - 2 - (tétrahydrofuran - 2 - yl)benzènesulfonamide; le N - [(4 - méthoxy - 6 - méthyl - 1,3,5 - triazin - 2 - yl)aminocarbonyl] - 2 - tétrahydrofuran - 2 - -yl)benzènesulfonamide; ou un de leurs sels convenant pour l'agriculture.
15. Un composé selon la revendication 1, choisi parmi le N - [(4 - méthoxy - 6 - méthylpyrimidin - 2 - yl)aminocarbonyl] - 2 - (2 - pyridinyl)benzènesulfonamide; le N - [(4,6-diméthylpyrimidin - 2 - yl)aminocarbonyl] - 2 - (2 - pyridinyl)benzènesulfonamide; le N - [(4,6-diméthoxy - pyrimidin - 2 - yl)-aminocarbonyl] - 2 - (2 - pyridinyl)benzènesulfonamide; ou un de leurs sels convenant pour l'agriculture.
16. Un composé selon la revendication 1, qui est le N - [(4 - méthoxy - 6 - méthylpyrimidin - 2 - yl)aminocarbonyl] - 2 - (2 - pyrimidinyl)benzènesulfonamide; ou un de ses sels convenant pour l'agriculture.
17. Une composition utilisable pour lutter contre le croissance de végétation indésirable comprenant une quantité efficace d'un composé à activité herbicide et au moins un des ingrédients suivants; agent tensio-actif, diluant solide ou liquide, caractérisée en ce que le composé à activité herbicide comprend un composé selon l'une quelconque des revendications 1 à 16.
18. Un procédé de lutte contre la croissance de végétation indésirable en appliquant au lieu à protéger une quantité efficace d'une composé à activité herbicide, caractérisé en ce que le composé à activité herbicide comprend un composé selon l'une quelconque des revendications 1 à 16.
19. Un procédé pour régler la croissance de plantes en appliquant au lieu de ces plantes une quantité efficace, mais substantiellement non-phytotoxique, d'un agent de réglage de la croissance de plantes, caractérisé en ce que l'agent de réglage de la croissance des plantes comprend un composé selon l'une quelconque des revendications 1 à 16.
20. Un procédé de préparation d'un composé de la revendication 1, qui comprend
(a) la réaction d'un benzènesulfonamide de formule
Figure imgb0239
avec un méthyl hétéroaryl carbamate de formule
Figure imgb0240
en présence d'une quantité équimolaire de triméthylaluminium pour obtenir un composé de formule (I) où R1, R17, Q et A sont tels que définis dans la revendication 1 et W est O; ou
(b) la réaction d'un isocyanate ou isothiocyanate de benzènesulfonyle de formule
Figure imgb0241
avec un aminohétérocycle de formule
Figure imgb0242
où R1, R17, W et A sont tels que définis dans la revendication 1 et Q est choisi parmi Q-1, Q―2 ou Q-6 à Q-11; ou
(c) la réaction du sulfonamide de formule (II) avec un isothiocyanate hétérocyclique de formule
Figure imgb0243
où A est tel que défini dans la revendication 1; ou
(d) la réaction d'un sulfonamide de formule
Figure imgb0244
avec un méthyl pyrimidinyl carbamate ou un méthyl triazinyl carbamate de formule
Figure imgb0245
en présence d'une quantité équimolaire de triméthylaluminium, où R1, R17, Q', X, Y et Z sont tels que définis dans la revendication 1, pour obtenir un produit de formule (la).
EP83300078A 1982-01-07 1983-01-07 Sulfonamides à activité herbicide Expired EP0085476B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT83300078T ATE26715T1 (de) 1982-01-07 1983-01-07 Herbizide sulfonamide.

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US33793382A 1982-01-07 1982-01-07
US337933 1982-01-07
US437325 1982-10-28
US06/437,325 US4494980A (en) 1982-10-28 1982-10-28 Herbicidal ortho-(azinyl)-benzenesulfonamides
US06/437,367 US4460401A (en) 1982-01-07 1982-11-01 Benzenesulfonamides as herbicides
US437367 1982-11-01

Publications (3)

Publication Number Publication Date
EP0085476A2 EP0085476A2 (fr) 1983-08-10
EP0085476A3 EP0085476A3 (en) 1984-06-27
EP0085476B1 true EP0085476B1 (fr) 1987-04-22

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP83300078A Expired EP0085476B1 (fr) 1982-01-07 1983-01-07 Sulfonamides à activité herbicide

Country Status (8)

Country Link
EP (1) EP0085476B1 (fr)
JP (1) JPS58121283A (fr)
AU (1) AU551721B2 (fr)
BR (1) BR8300016A (fr)
DE (1) DE3371078D1 (fr)
DK (1) DK3883A (fr)
GB (1) GB2112784B (fr)
GR (1) GR77171B (fr)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0101670B1 (fr) * 1982-08-23 1988-03-09 Ciba-Geigy Ag Procédé de préparation de sulfonylurées ayant une activité herbicide et régulatrice de croissance de plantes
EP0111442A1 (fr) * 1982-11-12 1984-06-20 Ciba-Geigy Ag N-2-hétérocyclyl-phénylsulfonyle-N'-pyrimidinyl- et -triazinyl-urées
US4604131A (en) * 1983-08-05 1986-08-05 E. I. Du Pont De Nemours And Company Herbicidal sulfonamides
US4705556A (en) * 1984-07-12 1987-11-10 E. I. Du Pont De Nemours And Company Herbicidal sulfonamides
US4602936A (en) * 1983-09-09 1986-07-29 Ciba-Geigy Corporation Herbicidal sulfonylureas
AU585761B2 (en) * 1984-03-07 1989-06-22 E.I. Du Pont De Nemours And Company Herbicidal fluoroethoxy triazines
EP0158600B1 (fr) * 1984-04-11 1991-04-03 Ciba-Geigy Ag Procédé de lutte sélective contre les mauvaises herbes dans les cultures de plantes utiles
US4637829A (en) * 1984-04-27 1987-01-20 Ciba-Geigy Corporation Sulfonylureas
EP0164269B1 (fr) * 1984-06-07 1990-04-18 E.I. Du Pont De Nemours And Company Sulfonamides herbicides
US4684393A (en) * 1984-06-11 1987-08-04 E. I. Dupont De Nemours And Company Herbicidal thiophenesulfonamides
AU576868B2 (en) * 1984-06-11 1988-09-08 E.I. Du Pont De Nemours And Company Thiophene and pyridine sulfonamides
AU578307B2 (en) 1984-09-17 1988-10-20 E.I. Du Pont De Nemours And Company Herbicidal pyrazolesulfonamides
AU4789685A (en) * 1984-09-28 1986-04-10 E.I. Du Pont De Nemours And Company Heterocyclic sulphonamide derivatives
US5017214A (en) * 1985-05-30 1991-05-21 George Levitt Herbicidal sulfonamides
US4913726A (en) * 1985-05-30 1990-04-03 E. I. Du Pont De Nemours And Company Herbicidal sulfonamides
DE3677652D1 (de) 1985-05-30 1991-04-04 Du Pont Herbizid wirksame sulfonamide.
US4741765A (en) * 1986-01-30 1988-05-03 E. I. Du Pont De Nemours And Company Herbicidal sulfonamides
US4902339A (en) * 1986-03-26 1990-02-20 E. I. Du Pont De Nemours And Company Herbicidal sulfonamides
JPS62242679A (ja) * 1986-04-11 1987-10-23 イ−・アイ・デユポン・デ・ニモアス・アンド・カンパニ− スルホニル尿素化合物
JP2598317B2 (ja) * 1989-02-08 1997-04-09 呉羽化学工業株式会社 Ｎ‐置換‐３‐（含窒素５員環）ベンゼンスルホンアミド誘導体、その製造方法及び除草剤
US5242894A (en) * 1989-02-08 1993-09-07 Kureha Kagaku Kogyo K.K. N-substituted-3-(nitrogen-containing 5-membered ring)-benzenesulfonamide derivatives, and herbicidal compositions
JP4632549B2 (ja) * 1999-04-23 2011-02-16 ピジョン株式会社 学習用飲料カップ

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0030139A2 (fr) * 1979-11-30 1981-06-10 E.I. Du Pont De Nemours And Company Urées et isourées à activité herbicide, leur préparation et leur utilisation, et compositions les contenant

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK401978A (da) * 1977-10-06 1979-04-07 Du Pont Herbicide sulfonamider
DK37880A (da) * 1979-02-22 1980-08-23 Du Pont Herbicide sulfonamider

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0030139A2 (fr) * 1979-11-30 1981-06-10 E.I. Du Pont De Nemours And Company Urées et isourées à activité herbicide, leur préparation et leur utilisation, et compositions les contenant

Also Published As

Publication number Publication date
DK3883A (da) 1983-07-08
DK3883D0 (da) 1983-01-06
GR77171B (fr) 1984-09-10
AU551721B2 (en) 1986-05-08
EP0085476A3 (en) 1984-06-27
BR8300016A (pt) 1983-08-30
EP0085476A2 (fr) 1983-08-10
GB8300366D0 (en) 1983-02-09
JPS58121283A (ja) 1983-07-19
DE3371078D1 (en) 1987-05-27
GB2112784A (en) 1983-07-27
GB2112784B (en) 1986-02-26
AU1021183A (en) 1983-07-14

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